These 5 Caribbean Cities Are Perfect for a Quick Weekend Getaway

The Caribbean is about more than just its stunning natural beauty — it’s about culture, character, and city streets that feel like they’ve lived a hundred lives. Some of the most memorable escapes happen not on a remote cay, but in a historic square, a buzzing market, a tucked-away jazz bar. These five Caribbean cities offer that kind of experience — immersive, energizing, and unforgettable. And with just a weekend, you can catch their rhythm — especially if you stay in the right place.

Here are five great spots in the Caribbean for a weekend getaway — and thanks to easy flights from places like Miami and New York, each of these places is close enough for a totally doable, enjoyable two or three-day Caribbean vacation. We’ve also included a quick-bite tip for one memorable thing to do in each city during your stay.

Nassau, The Bahamas

This is a city that rewards exploration. Step past the cruise port and you’re in a world of pastel facades, centuries-old forts, and rhythmic street corners. The real Nassau unfolds when you wander. Start with a walk down Bay Street, duck into the National Art Gallery for a cultural primer, then cross over to West Bay and the sounds and smells of something purely Bahamian. And you have to experience the dynamic bar scene in the capital, too. And then the worlds of experiences at Atlantis and Baha Mar (including Jon Batiste’s exceptional new jazz club) are just a quick cab ride away.

One Cool Experience: The Fish Fry at Arawak Cay

This is where you taste The Bahamas. A collection of colorful shacks and open-air stalls, the Fish Fry is where you go for fresh conch salad, fried snapper, and Kalik beer — served with live music and zero pretension. It’s loud, joyful, and entirely local.

Where to Stay: Graycliff Hotel

Graycliff isn’t just a hotel — it’s part of the city’s story. This 18th-century mansion offers a kind of classic luxury you don’t find much anymore: wood-paneled dining rooms, vintage wine, and cigars rolled on site. Set just up the hill from the city center, it’s close to everything yet completely removed, like a secret hideaway. Wander the gardens, sip rum by the pool, and let the old-world charm do its work. The best part is everything in the heart of downtown is just a short stroll. Rooms from $456.

Willemstad, Curacao

Willemstad is a mood: vibrant, artsy, full of unexpected turns. One moment you’re on the Queen Emma Bridge watching boats drift through the bay, the next you’re in Pietermaai sipping something under a canopy of twinkle lights (or trying the city’s incredible french fries).

The Dutch Caribbean aesthetic blends effortlessly with Caribbean soul, creating a city that’s as fun as it is photogenic. And it’s as walkable as place as you’ll find in the Caribbean. 

One Cool Tip: A Green Rum at Netto Bar

This legendary bar in Otrobanda is a local institution — and its claim to fame is the locally distilled, bright green rum. It’s strong, sweet, and unforgettable, especially in the company of regulars who treat visitors like friends.

Where to Stay: Brion City Hotel

Perched right by the water in Otrobanda, the Brion City Hotel delivers some of the best views in the city — the iconic skyline glowing across the bay. Rooms are modern, clean, and efficient, and the elevated pool is the kind of unexpected luxury that makes a long weekend feel just a little longer. Step outside and you’re in the thick of things — cafes, murals, music — everything that makes Willemstad a living postcard. The best part? You can find rooms right now for just $97 per night.

Santo Domingo, Dominican Republic

This isn’t just a capital city. It’s the beginning of the Americas — and it carries that weight with swagger. The Zona Colonial is a maze of stone alleys, faded facades, and churches that have been standing since Columbus. But this city also pulses with modern energy — stylish locals, bold cuisine, and a scene that’s as comfortable in a wine bar as it is at a roadside empanada cart.

One Cool Experience: Exploring the Zona’s Art Galleries
Amid the 500-year-old walls are a growing number of contemporary galleries showcasing Dominican artists. Places like Distrito Del Arte bring texture and perspective to a city that has never stopped reinventing itself.

Where to Stay: Kimpton Las Mercedes Santo Domingo

This is what boutique luxury looks like in the oldest city in the New World. Set in a restored historic building with contemporary flair, the Kimpton, which opened its doors last year, offers the best of both Santo Domingos: timeless bones and modern style. Rooms are light-filled and curated, the rooftop has panoramic views, and the location lets you slip from colonial charm to cosmopolitan buzz in minutes. And yes, there’s a rooftop lounge. Rooms from $152, according to Google Hotels.

Old San Juan, Puerto Rico 

There’s something cinematic about Old San Juan — maybe it’s the cobblestone streets, the colonial-era colorful balconies, or the way the light hits the harbor at dusk. But this is far more than a photo op. It’s a living, breathing city that hums with energy and flavor. You just need to venture, eat, drink, listen, and let the island guide you.

One Cool Thing to Do: Live Jazz at Carli’s Fine Bistro & Piano

Tucked into a corner of Plaza Colón, Carli’s is where the locals go for piano jazz, great food, and the occasional celebrity cameo. Owned by former Beach Boys keyboardist Carli Muñoz, it’s equal parts restaurant, club, and cultural institution.

Where to Stay: Palacio Provincial

With high ceilings, lush courtyards, and a rooftop that seems to float above the city, Palacio Provincial is where grown-up travelers land. The hotel blends timeless elegance with thoughtful design, just steps from the city’s best shops, museums, and nightlife. Whether you’re lounging by the rooftop plunge pool or sipping espresso in the lobby, this is the San Juan of your long weekend dreams. It’s also got one of the best bars in the city. Rooms from $237.

Kingston, Jamaica

Kingston challenges you to be a better traveler— and that’s the magic. It’s a city of contrast: gritty and graceful, kinetic and introspective. You come here for the music, the history, the food, but you stay for the momentum — for the feeling that this is the real Jamaica, and it’s always pushing forward.

One Cool Adventure: Explore Kingston’s Art Scene

Kingston Creative has been telling the story of the city’s cultural rebirth and exploding art scene for years now, and the organization offers regular walking tours to immerse yourself in this dynamic movement. It’s a great way to enjoy some of the most stunning artwork on the island.

Where to Stay: AC Hotel Kingston

Sleek, modern, and centrally located, the AC is where Kingston’s creative class and international visitors converge. It’s got the feel of a New York boutique hotel — clean lines, minimalist rooms, a pool that has one of the hottest scenes in the capital — with a distinctly Jamaican personality. Grab a coffee, take a dip or sip a rum old fashioned at the bar. Rooms from $276.

These cities won’t ask for much of your time. Just a weekend, or a few open hours. A willingness to follow the music, the color, the scent of street food. That’s all it takes — and suddenly you’re in it. Living the Caribbean.